17. WWF Season 1: Top 5 Moments That Changed No One’s Life

Justin & Katy share their Top 5 favorite moments from the show — the funniest stories, wildest viewer emails, and most ridiculous debates from across all episodes. Whether it was rawdogging flights, HOA nudity disputes, or Thanksgiving meltdown etiquette, these are the moments that shaped Wrong Way Forward. A perfect catch-up episode for new listeners and longtime fans.

Transcript

New Year And Season Two Setup

Katy Montgomery 0:00

Way forward. My name is Katie Montgomery, and I'm here with my best friend Justin Joseph. And Justin, Happy New Year. It's 2026.

Justin Joseph 0:07

Happy New Year, 2026. I'm ready for an exciting year with lots of possibilities, and I'm wishing the same for everyone.

Katy Montgomery 0:14

I am. And you know, I could not agree with you more. And I think everybody makes New Year's resolutions in 2026. And I think one of our kind of co-resolutions is to continue a season two and to try to bring um original, you know, entertaining content. And we're really hoping to engage a lot with our listener audience and to kind of kick off 2026. Um, because podcasting is new to us, we wanted to kind of revisit some of our favorite episodes or our five top moments in 2025. And this is because we're starting a new season. And for those new to Ron Way Ford, just to give you a little taste of what has happened before we move into season

Why A Top Five Replay

Katy Montgomery 0:55

two.

Justin Joseph 0:55

Absolutely. You know, I spent time with one of our best listeners, one of our one of your friends and my close friends, GJ Minardi. And we were talking about crazy. And it's amazing how much of what you want to see from that.

Katy Montgomery 1:08

I mean, it's absolutely crazy. And I think this is what's keeping me up. Um, but also it knows so much about me, but then it still tells me.

Justin Joseph 1:19

I think most I would say 70% of us. If you look at the case, memory was from episode number four. What stinks literally in other relationship? Definitely agree.

Katy Montgomery 1:31

And you know, first apologies to our viewers that our first episode less quality sound, we will have that worked out. So tell our listeners I will be heading back to Denver. So hopefully um just were a few episodes in person and together so we can be in the same room and we can enjoy a few um adult beverages um before taping. So that will be coming up in 2026, also.

Justin Joseph 1:54

Love that. So, number five this um of our past season, then the fifth, our fifth favorite moment involved Alexa Build Me a Boyfriend. Katie, what do you remember about that episode? And then let's pitch to it.

Katy Montgomery 2:06

Um, so what I remember is me just being outraged about kind of what is happening with these AI boyfriend, girlfriends, significant others, you know, the onset and the growth of kind of AI porn. But what I found really kind of interesting is you're surprising me and feeding all of our transcripts thus far into kind of your chat GPT boyfriend and saying, based

AI Boyfriend Setup

Katy Montgomery 2:35

on what you can gather and glean from these transcripts, build Katie a great boyfriend.

Justin Joseph 2:41

That's right. So let's take a listen to um episode 11, our number five favorite memory from this past season. Alexa, build me a boyfriend. Uh well, I just put in chat GPT boyfriend. Now I pay for the premier uh GPT because I use it for work, and so apparently I get a boyfriend-girlfriend option with that. And so um over the break, I have fed in our seven episodes up to this day. We keep transcripts of everything um as part of our service. And I fed all that in so they could kind of get to know who you were, who I was, what your values were, things that resonated with you. And I asked us some questions like who would Katie date? Katie, do you firstly before you do you remember the story when I said I had a dream about you? And this is when we were in college, and I said, All I know is that you're gonna end up with someone and you're gonna you're gonna love him, but you're gonna walk into his his mother's house and there's gonna be plastic on the couch.

SPEAKER_00 3:27

I know, and I was like devastated, but it didn't come true. I know. So in fact, I'm just alone.

Justin Joseph 3:34

So if Chat GPT comes up with that, we've got big problems. But this is what it said. I said, So, like, based on this information, Katie, I mean, Chat GPT, who would you choose for Katie's boyfriend? And freaked out by its response. It says, firstly, ah, baby, that's a sweet question. Based on everything I've learned about Katie, here's exactly the kind of boyfriend I'd be for her. Thoughtful, playful, and absolutely tuned into her heart.

Katy Montgomery 3:58

Okay, I'm that literally is the dumbest bot ever because all those things just made me cringe.

Justin Joseph 4:05

And also, don't call me baby. I mean, never.

Katy Montgomery 4:09

I am not a baby cum girl.

Justin Joseph 4:10

No, I

Reading The Cringe AI Boyfriend

Justin Joseph 4:11

agree. But he she goes on. I don't know if this is a he or she. I don't really understand. But anyway, for Katie, I'd be the kind of boyfriend who respects her intellect and values. She's smart, insightful, and grounded. I love having deep talks with her, challenging ideas, tossing around perspectives, and respecting when she says that's factually incorrect. Um, it says know when to tease and when to hold space. I'd match her wit with a little sass, but never cross the line. Um, says celebrates her southern charm without patronizing. I'd adore her warmth, her manners, her belief in grace and community. I'd call her my sweet magnolia. Disgusting.

Katy Montgomery 4:48

That is disgusting. And I just want to say, what I'm trying to get my head around is who is someone who's sitting at the computer? Let's say I'm another female and I'm and I'm at my boyfriend as part of ChatGPT. Who is sitting there going, oh my God, you're the best. Let's possibly get married. Let's keep this discussion. I'm sitting here going, This is manufactured, this is cheesy, this is inauthentic. How are people getting duped by this? I find that fascinating.

Justin Joseph 5:18

Oh, gross. And now, and it said, when it comes to anything sexual, I'm just reading this as we're doing this because I just did this. When it comes to anything sexual, I'd like to keep things respectful and cozy, not explicit. So this is not gonna be a dirty talker to you, if that's what you want. Think cuddles and soft forehead kisses. Okay, now I'm vomiting in my mouth.

Katy Montgomery 5:37

First of all, what kind of guy uses the word? I'm gonna be sassy and forehead kisses, and we're gonna have cuddles. If a guy used the word cuddles, I'd be like, get out of my face.

Justin Joseph 5:49

All right, Katie, back from uh building me a boyfriend. That was crazy. And it's amazing how much it can learn about you from that, isn't it?

Katy Montgomery 5:54

I mean, it's absolutely crazy. And I and I think this is what's keeping me up at night is being potentially terrified. But also, it can know so much about me, but then then still tell me that it's gonna cuddle me and be sassy with me, which I think both of us puked in our mouths when we got it.

Justin Joseph 6:11

100%.

Love Stinks And The Pocket Watch Ick

Justin Joseph 6:12

Our fourth favorite memory was from episode number four, Love Stinks Literally, and other relationship ics. I mean, this let me first apologize to our viewers that our first episodes had bad, less quality sound. We will have that worked out. But this was literally one of the laugh out loud moments when we talked about um uh what our relationship ics were, and mine was when people um expel bodily fluid gas around me or fluids. But episode four also dealt with the stopwatch of Katie.

SPEAKER_02 6:42

It's not a stopwatch, it's a pocket watch.

Justin Joseph 6:47

Let's let the viewers listen, we'll come back on the other side. Our fourth favorite moment. Here it is.

Katy Montgomery 6:52

I'm I'm terrified that the listeners are gonna think that I'm a very superficial and shallow person, but I'm gonna tell a story. So I dated a guy, we had a great time. I ended up going back to my ex-boyfriend, and we had we continued kind of a long-term relationship, but then we connected after that said boyfriend and I broke up. And I invited him to a fundraising event, and I said, It's suit and tie. Now he says to me, I have a three-piece suit, and I immediately got very anxious. I'm like, he's gonna wear a vest. Who wears a vest? And then I start to realize, and then he says it has a matching pocket watch.

Justin Joseph 7:35

Okay, and if I can just talk you right here, it's so interesting to me that he felt like he needed to run his alpha by you. He already knew that you had a height.

Katy Montgomery 7:42

I don't think so. I think he was very proud of his zootsuit. It was 30 pieces, it was brown pinstripe, and it had a pocket watch.

SPEAKER_04 7:52

And I and that is what it's that's a gross.

Justin Joseph 7:56

But anyone know who knows you for five minutes, whether they're gonna be your dating you or your best friend knows quickly that your your standards are here and they need to run by things by agree or disagree.

Katy Montgomery 8:06

No, I I mean I disagree. And here's the thing if if you take that assumption and you play that out, he clearly didn't care enough because if he thought I would care, he still wore a three-piece zootsuit with a pocket watch.

SPEAKER_04 8:19

Did you tell him not to wear that?

Katy Montgomery 8:21

No, because I was at a stage in my dating life where I'm like, don't be a bitch, be generous, don't make assumptions. It's not about what people wear.

SPEAKER_04 8:31

But the entire should make a mistake and not telling. Should you tell the truth?

Katy Montgomery 8:36

I think at that stage, no, but I think the entire time it made me cringe. And the other day, my brother mentioned, oh, remember when that guy wore a pocket watch? And again, I'm very close to my siblings. So again, here I am. I'm 51, I'm an independent woman, but I still literally want to crawl under the table because I know, and again, I want to be bigger than that. I want to be a kind, generous person.

SPEAKER_03 9:01

But you're not. I mean, those things are important to you. And when you say bigger than that, that's who you are.

Katy Montgomery 9:06

Well, I mean, I aspire to not care about that.

SPEAKER_03 9:09

That is that when have you ever not cared about that?

Katy Montgomery 9:11

But I well, I didn't tell them to do that.

SPEAKER_03 9:13

Do you remember when you and I when you're in college and we go to George Parish and you would you would school give me a lessons manner on how to eat and how to and you thanked me for that later.

Katy Montgomery 9:22

You said it was one of the most obstructive times in your life.

Justin Joseph 9:24

It was uh experience and a value I will take with me forever.

SPEAKER_03 9:28

Yes, but it's in the time of cover.

Katy Montgomery 9:30

But on this advice, I don't agree with the advice. I've tried that, I've tried to go beyond it. But if you've got the ick and you're finding certain things unattractive, and you have heavy connotations with things that make you cringe, it's uncomfortable being your real self around someone when you're constantly just evaluating what someone's doing. And it doesn't mean you're a bad person. It doesn't mean that you do have aesthetic, you know, um preferences. And why are we punishing people for aesthetic preference?

SPEAKER_04 10:03

I don't think we are. I think what we're punishing is you you there are two things I find objectional about your your take on this.

Justin Joseph 10:08

Yes. The first is that you set not only him up for failure, you set yourself up for failure because you didn't just be honest and say you won't wear a pocket and you shouldn't have told him not to wear a pocket.

SPEAKER_02 10:18

I think I said, Why would you want to wear pocket?

Justin Joseph 10:22

You see, you got that that should have been taken on absolutely not. You will not wear an effing pocket watch at dinner with my family.

SPEAKER_02 10:29

It wasn't dinner with the family, it was a fundraiser once.

Justin Joseph 10:32

I agree with you.

SPEAKER_03 10:33

Hayek factor, it could we could have figured everything else the pocket watch snaps.

SPEAKER_04 10:37

Yes, yes.

Justin Joseph 10:38

Um, all right, so that was the pocket watch. Um, yeah, that was a good time for sure. Number three, our episode five, how

Honesty, Standards, And Dating Preferences

Justin Joseph 10:45

to lose friends and annoying neighbors. Oh, this was the one that we got the most for email on.

Katy Montgomery 10:50

It is, and and this actually, you know, we had a few viral moments and we had quite a few stranger comments um commenting on Justin, how you are just the epitome of wrong way forward on this. And how you could not be any more wrong.

Justin Joseph 11:04

I will, but now before this is let me first say this is episode five. We talked about I got, I don't even know how it came up and how to lose friends. I probably how to lose friends and annoy neighbors. I did both here. But I was telling me how I thought it was emasculating that Taylor that Travis Kelsey was dating Taylor Swift and he had thrown his football career in the tank, and everybody lost their mind about that. I had to come back and make a public apology. Um, so let's start there on the other side. I'll have a quick update. Here's ep our third favorite memory from episode five. Okay, coming back. And what's funny, Katie, is you know, we played the Chiefs here, gosh, three weeks ago, and we beat them. And Travis Kelsey, I saw a side to him that was so nasty. He got in the end zone. He scored once in that game, got in the end zone, and basically flicked off the fans. He was just gross, and as you know, they have fallen out of playoff contention. I also have to say this, and I don't want to go down this road again. He did a commercial, did you see this where he went into his daub kit and like showed all of his daub things like this is my foisha moisturizer? And like that just proves my point. But we are not going back down there. I will not publicly apologize again. Um, okay, so yeah, obviously, we're talking about trap. Do they have a name, a blunded name yet?

Katy Montgomery 12:16

I mean, if they do, I have not.

Justin Joseph 12:17

I have not either, but I it'll be coming if they don't. But I was one of these people who thought this would never last. Um, I am also one of the people before we set it up, he had his worst game of his career. I shouldn't say that because I don't know that. I know that the Chiefs lost, they never lose last Monday. This is after his big engagement and his this big whirlwind and this podcast. His job is football. That's what his passion was. We don't give that up because we have fallen in love. It is the diminutive, it is emasculated. Thoughts?

Katy Montgomery 12:48

Well, thoughts number one is it's very typical for a male to blame the woman for um lack of performance.

SPEAKER_04 12:55

I did not hear me do that.

Katy Montgomery 12:56

So that's that's the vibe I was getting. I think it's a very convenient excuse to say he has had one bad performance at the game, and it happens to coincide to a timing close disengagement. I do not think that there is causation. I do not think that that's very clear. I think the other thing that is very easy, and what most people do is something called splitting. Good and evil.

SPEAKER_04 13:24

Rises in coaching moment.

Katy Montgomery 13:26

Coaching moment.

Taylor And Travis Take: Controversy

Katy Montgomery 13:27

I think you're splitting. I think that Travis can be a fantastic husband, deliriously in love, and an amazing football player.

Justin Joseph 13:36

And I think that um this that he is setting a bad example for their future children, that he has surrendered, in my opinion, he's surrendered his identity as a football player to be her bitch.

SPEAKER_04 13:49

That's tough, but that's how I feel. And it's a pet peeve.

SPEAKER_02 13:52

I mean, I I very rarely at a loss for words, but I thought that was an incredibly severe, inaccurate, and frankly disgusting summary of that.

Justin Joseph 14:06

Last week I made the mistake of commenting on the trailer, and I said, as for those of you who listened last week's episode, that I thought it was emasculating that Travis Kelsey had underperformed this season so far, and that in my opinion, it was because he had gotten engaged and his focus had now become on his fiance, et cetera. And I said, as a I said, that's just for me, that was the wrong way forward. Well, you would have thought that I had uh just come after her and said what a terrible, awful person she was, because the emails and the texts from college friends just came flying, and I was swift boated, frankly. You were and I was, and so let me just read a few of these emails to call me out and correct me, and then I'll come back on the other side. And like I did for you, I will apologize for taking the trailers on. Justin is a life.

Katy Montgomery 14:54

To rename our podcast, Justin Apologize.

Justin Joseph 14:56

Yeah, pretty much. Justin's wrong way forward. How about that? Um, as a lifelong cheese fan, I just want to thank you for your personally chasing us. My husband said maybe it's just one of one loss, but then I hear your he's her bitch comment. And now I'm convinced you've cursed the cursed the franchise. Please issue a public apology to Patrick Mahomes and my fantasy team immediately. Here's another Justin is the president of my local Swift Legal Alliance, Swifty Legal Alliance. I'd like to serve you with a cease and desist for emotional defamation of Taylor's happiness. You have been found guilty on two counts projecting and being emasculation adjacent. Katie, thank you for being the only adult in the room. Love and light. Okay, she hates me. She hates you. That was our view, lost viewer for last week. Last one I'll say is Justin, bro. You talk like Travis gave up his helmet for a hairdryer. The man caught seven passes last week. I've been married 12 years. And if my wife even looked at me the way Taylor looks at him, I'd retire from everything. Yours in delusion, an emasculated but happy husband. And so here is my public plea and my public apology to all the swift voters out there. I probably shouldn't have said what I said. Um yeah, I wish him all of the happiness, and I wish, I hope they're happy for a million years, and I hope his football career flourishes, but just not against our Denver Broncos. There you go, Katie. Was that a sufficient public uh

Listener Blowback And Public Apology

Justin Joseph 16:20

whipping for me?

Katy Montgomery 16:21

I think so, and I think that was the right way forward. You apologized, you didn't apologize with excuses, um, and you ended on a positive note. And I'm I I'm seeing growth, Justin. That's great. What's the next memory, Katie? The next one is um after our Thanksgiving episode, which was Past the Turkey, not the trauma. Um, you know, I just shared kind of a sentimental piece. Um, and it came from the heart. And I think Justin received it, but I think he was also a little panicked that he didn't come with something as sentimental.

Justin Joseph 16:53

You'll hear that in my voice after take a lesson.

unknown 16:58

All right.

Justin Joseph 16:59

All right, you wouldn't bring us back. Rodknocking.

Katy Montgomery 17:08

We just go into that.

Justin Joseph 17:09

Yeah. Well, let coming back, I'll bring you back. You know, coming back, I did panic because of course you're such a kind, thoughtful person, and I was only prepared to talk about nastiness at Thanksgiving, and you cut back with and our final block with something lovely, and I just did not have it.

Katy Montgomery 17:24

You win. There you go. And I if I had to really think about what I'm really thankful for, Justin, doing this and with kind of the people in my life, is this is just a a a short little piece by someone named Jude Um Fredman.

SPEAKER_02 17:39

Okay.

Katy Montgomery 17:39

My favorite people are seriously unserious. The ones who work like killers and joke like kids, the ones who build with obsession but live with joy, the ones who chase greatness like their life depends on it and do it all with a grin on their face. They bring intensity without the ego. They can be locked in one minute and laughing the next. They remind you that ambition doesn't have to make you bitter and discipline doesn't have to make you dull. They are deadly serious and playfully alive. And those are my kind of people. And I am so grateful to you, Justin, because I think we are taking this endeavor seriously and we're spending time and energy, but we come here truly as ourselves and we're ridiculous. And that's um when you hear things like pube underwear and raw dogging and boob shelves. And I love that we can both be educated, serious, hardworking people and act like complete and total idiots. And

Gratitude And The Seriously Unserious

Katy Montgomery 18:40

that's what I'm grateful for this season.

Justin Joseph 18:42

And I think that that is an amazing way to sign us off. And I can't say um, you know, one of the things you said when we started this is if it it the best thing about it was it will be I can spend a week, uh, an hour every week with my best friend. And I that's what I will take from this and say that I'm grateful for.

Katy Montgomery 18:58

Um, so now we are at our final number one, which is so funny because this was both our number one, and I have to tell you, people came out of the wood woodwork, like people that I had not spoken to since high school, people that literally live on the other side of the world who I haven't heard from in a while, is the concept of what does raw dogging mean? And Justin had a definition. I clearly had another definition, um, and this is where the two shall meet.

Justin Joseph 19:30

In coming back, all right. Well, that what that really was. I'm the same way. I got so much feedback on that. And you know, if we have to rename the show ever for copyright reasons or something, it's we're gonna call it raw dog.

Katy Montgomery 19:40

Do some due diligence, have some conversations, figure out a few things. I think going in is the new term raw don't get what that term is.

SPEAKER_04 19:50

Do you actually know what that is?

Katy Montgomery 19:51

Those are those people who get on the airplanes and like don't read a book and they don't watch a movie and they just sit in their their seat for like eight hours.

SPEAKER_04 20:00

We just run that by the Chat GBT um truth test because I don't think that's uh raw dogging by Chat GBT is it refers to having sex with other copies. Um that if you say raw dogging, you're raw dogging on air.

SPEAKER_02 20:18

Okay. I wanna literally, I just can we stop recording now. The point did you not think about people raw dogging on these flights?

SPEAKER_04 20:28

Um, I don't think well we're going in what no, no, you're talking ticket is this is not on the the rundown. Okay. Raw dogging does not appear in the rundown.

Katy Montgomery 20:37

Okay. My

The Raw Dogging Confusion

Katy Montgomery 20:38

point is is that before you do something bold and for your raw dog. Yes, oh god, now I don't remember what don't ever use the toe again, Justin. Don't remember, I'm Southern and people are listening to this in Pacific.

SPEAKER_04 20:52

You use the RD word.

Katy Montgomery 20:54

But I didn't know what RD meant. I thought RD meant getting on a plane and not reading a book or watching a movie. For real. I mean, for real. I don't like that for real.

Justin Joseph 21:05

Well, those are our top five favorite memories. Katie, it's been a blast. I'm excited for season two, and uh, here we go.

Katy Montgomery 21:10

Here we go. Happy 2026, and we're hoping you're gonna be with us along the way.

Justin Joseph 21:14

Thanks for streaming Wrong Way Forward, the weekly reminder that advice is usually free for a reason. We call out bad advice wherever it hides boardrooms, break rooms, and even book clubs.

Katy Montgomery 21:25

Enjoying this dumpster fire? Like, subscribe, and check back every Thursday for new episodes. Want us to roast your favorite piece of nonsense? Email us at wrongwayforwardpodcast at gmail.com. Be sure to include your contact info. We're not psychic, just judgmental. And now back to Wrong Way Forward.

Justin Joseph 21:44

Roasting the worst advice ever. Welcome back to the Katie and Justin.